Synthesis and properties of soluble poly[bis(benzimidazobenzisoquinolinones)] based on novel aromatic tetraamine monomers

Wang, Junhua; Li, Nanwen; Zhang, Feng; Zhang, Suobo; Liu, Jia

doi:10.1016/j.polymer.2008.12.007

Cited by 12 publications

(5 citation statements)

References 18 publications

(19 reference statements)

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“…Polymers with high free volume and rigidity are required for gas separation membranes in order to increase the selectivity and permeability simultaneously. − For this, bulky groups, such as methyl, tert -butyl, trifluoromethyl silanes, are commonly introduced into the main chain; decreasing the packing between chains, increasing the fractional free volume (FFV) and the permeability; − additionally, such modification reduces the segmental mobility, facilitates behavior as molecular sieves, and, hence, promotes high selectivity. , …”

Section: Introductionmentioning

confidence: 99%

“…10−14 For this, bulky groups, such as methyl, tert-butyl, trifluoromethyl silanes, are commonly introduced into the main chain; decreasing the packing between chains, increasing the fractional free volume (FFV) and the permeability; 15−19 additionally, such modification reduces the segmental mobility, facilitates behavior as molecular sieves, and, hence, promotes high selectivity. 20,21 This article reports the synthesis of custom-designed monomers (diamines) which give PIs with improved gas separation performance. 14,22−24 Our strategy was focused on significantly increasing the rigidity of the macromolecular chains by introducing biphenyl and methyl-substituted biphenyl units into the diamine structures.…”

Section: Introductionmentioning

confidence: 99%

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Fluorinated Biphenyl Aromatic Polyimides for Gas Separation Applications: Real Gas Mixture Study

Rico-Martínez,

Rojas-Rodriguez,

Esteban

et al. 2024

Ind. Eng. Chem. Res.

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Three aromatic polyimides (PIs) based on diamines containing a biphenyl unit and CF 3 -groups in the m-position to amines and 6FDA of high-molecular weights were synthesized. The polymers differed by number of methyl-substituents in the biphenyl moiety, as 6FDA-BFAPB, PI without methyl substituents, 6FDA-4MeBFAPB, PI with four methyl groups, and 6FDA-4MeBFAPB, PI with six methyl groups. The comparative analysis of the polymer properties was performed with focus on their gas transport properties. All PIs demonstrated high thermostability, with decomposition temperature above 450 °C in an inert atmosphere and char yield of 45−50% but were readily soluble at room temperature even in common organic solvents. The T g 's of PIs bearing methyl groups were notably higher than that of 6FDA-BFAPB, indicating their more rigid backbone chains. Detailed investigation of the PIs' gas transport properties was also made for pure gases and real gas mixture in the wide interval of pressures. It was shown that introduction of the methyl substituents in the main polymer chain resulted in an important improvement of the gas transport properties; both methylated PIs were located much closer to the Robeson limit.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Fluorinated Biphenyl Aromatic Polyimides for Gas Separation Applications: Real Gas Mixture Study

Rico-Martínez,

Rojas-Rodriguez,

Esteban

et al. 2024

Ind. Eng. Chem. Res.

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“…PPys resulting from ester‐, amide‐, and ether‐containing dianhydrides with aromatic tetraamines have been developed to improve their solubility and flexibility. Zhang and coworkers prepared tetraamines with flexible ether linkages by a two‐step procedure from bisphenols using nucleophilic substitution of bisphenol with 5‐chloro‐2‐nitroaniline, followed by a reduction in the nitro groups. Organo‐soluble poly(bis(benzimidazobenzisoquinolinones)) are prepared from the diether tetraamines and bis(naphthalic anhydrides).…”

Section: Introductionmentioning

confidence: 99%

Facile synthesis of high‐performance poly(pyrrolone imide)s from an unsymmetric phosphinated triamine

Lin

Hsu

et al. 2013

J. Polym. Sci. Part A: Polym. Chem.

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High‐performance and flexible poly(pyrrolone imide)s (PPyIs) were firstly prepared by the reaction of dianhydrides with an unsymmetric phosphinated triamine, 1‐(3,4‐diaminophenyl)‐1‐(4‐aminophenyl)‐1‐(6‐oxido‐6H ‐dibenz <1,2> oxaphosphorin‐6‐yl)ethane (1), which was prepared by a facile, one‐pot procedure from the reaction DOPO, 4‐aminoacetophenone in excess o‐phenylenediamine in the presence of p‐toluenesulfonic acid. Thermal properties of the resulting PPyIs were evaluated and compared with those of phosphinated polyimides with a similar structure. All of the prepared PPyIs films are tough and creasable. They display higher Tg (374–412 °C), lower coefficient of thermal expansion (34–46 ppm/°C), and better thermal stability (Td 5 wt %: 456–477 °C, 800 °C char yield: 59–63%) than analogous phosphinated polyimides. © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 2709–2715

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“…Also we can deduce that the alkaline‐hydrolysis resistance of these PPys would be destroyed because the amide or ester groups were frangible to alkaline. Similarly, Wang et al have designed four aromatic tetraamine monomers possessing flexible ether linkages and the resulting PPys were completely soluble in phenolic solvents …”

Section: Introductionmentioning

confidence: 99%

Fluorinated polybenzimidazopyrrolones with excellent alkaline‐hydrolysis resistance

Tao

Liu

Fan

et al. 2013

J of Applied Polymer Sci

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polybenzimidazopyrrolones (polypyrrolones, PPys) were synthesized via a two-step polycondensation procedure. The inherent viscosities of the precursors, poly(amide amino acid) (PAAA), ranged from 0.39 dL/g to 0.54 dL/g. All the FPPys were amorphous. The freestanding FPPy films could be prepared, which exhibited good thermal stability with the glass transition temperature of 315-389 C, the temperatures of 5% weight loss (T 5% ) of 497-535 C in nitrogen and residual weight retention at 700 C over 60%. All the FPPy films exhibited excellent alkaline-hydrolysis resistance which retained their original shapes and toughness after boiling 7 days in 10% sodium hydroxide solution. Also after boiling 8 h in 10% sodium hydroxide solution, the tensile strength could retain as high as 56% of the original values. The alkaline-hydrolysis resistance was much better than the polyimides which had similar chemical structures.

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Synthesis and properties of soluble poly[bis(benzimidazobenzisoquinolinones)] based on novel aromatic tetraamine monomers

Cited by 12 publications

References 18 publications

Fluorinated Biphenyl Aromatic Polyimides for Gas Separation Applications: Real Gas Mixture Study

Fluorinated Biphenyl Aromatic Polyimides for Gas Separation Applications: Real Gas Mixture Study

Facile synthesis of high‐performance poly(pyrrolone imide)s from an unsymmetric phosphinated triamine

Fluorinated polybenzimidazopyrrolones with excellent alkaline‐hydrolysis resistance

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